(Sp,S,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane

Base Information

• Chemical Name: (Sp,S,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane
• CAS No.: 1096144-06-7
• Molecular Formula: C₃₂H₃₃O₆P
• Molecular Weight: 544.584

Synonyms:(Sp,S,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane

Chemical Property of (Sp,S,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane

Chemical Property:

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Technology Process of (Sp,S,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane

There total 3 articles about (Sp,S,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 7.8%

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) + ethyl Phenylphosphinate (172487-18-2,2511-09-3) → (Sp,S,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane (1096144-06-7)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃;

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) + ethyl Phenylphosphinate (172487-18-2,2511-09-3) → (Sp,S,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane (1096144-06-7) + (Sp,R,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane (1096144-07-8) + (3S)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2R)-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane (1386972-34-4) + (3R)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2R)-phenyl-2-oxo-(2λ5)-[1,2]oxaphosphinane (1386972-35-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jm201428a

Reference yield:

→ (Sp,S,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane (1096144-06-7) + (Sp,R,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane (1096144-07-8)

Guidance literature:

upstream raw materials:

2,3,5-tri-O-benzyl-D-arabinofuranose

ethyl Phenylphosphinate

Downstream raw materials:

(Sp,S,S,S,R)-3-acetate-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane

(Sp,S,S,S,R)-3-benzyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane

(Sp,S,S,S,R)-3-benzoate-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane

(Sp,S,S,S,R)-3-trifluoroacetate-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane

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